Electric Literature of 154237-70-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 154237-70-4, name is 4-Bromo-3-cyanopyridine. A new synthetic method of this compound is introduced below.
3-Cyano-4-(phenylethynyl)pyridine (35). Copper(l) iodide (9.6 mg, 0.05 mmol), bis- (triphenylphosphine)palladium(ll) dichloride (29 mg, 0.025 mmol) and sodium ascorbate (9.9 mg, 0.05 mmol) were placed in a flask, which was degassed and filled with argon. Triethylamine (5.0 mL) was added, followed by 4-bromo-3-cyanopyridine 34 (92 mg, 0.5 mmol) in tetrahydrofuran (5.0 mL). The mixture was stirred at 40C for 30 min. Phenylethyne (76.5 mg, 0.75 mmol) was added and the mixture was stirred at 40C for 10 h. Evaporation and chromatography (petroleum ether / ethyl acetate 3: 1) gave 3-cyano-4-(phenylethynyl)pyridine 35 (80 mg, 78%) as an off-white powder: mp 74-75C (lit.91 85-87C); IR vmax 2222 (C?N), 2150 (C?C), 1582 (C=CAr), 1495 (C=N) cm”1; 1H NMR (CDCI3) delta 7.39-7.43 (3 H, m, Ph 3,4,5-H3), 7.45 (1 H, d, J = 5.2 Hz, 5-H), 7.63 (2 H, d, J = 8.2 Hz, Ph 2,6-H2), 8.75 (1 H, d, J = 5.2 Hz, 6-H), 8.87 (1 H, s, 2-H); 13C NMR (CDCI3) (HSQC / HMBC) delta 83.50 (ethyne 2-C), 101.29 (ethyne 1-C), 1 1.74 (4-C), 1 15.54 (C?N), 120.76 (Ph 1-C), 125.06 (5-C), 128.59 (Ph 3,5-C2), 130.28 (Ph 4- C), 132.38 (Ph 2,6-C2), 134.87 (3-C), 152.40 (2-C), 152.68 (6-C); MS m/z 227.0569 (M + Na)+ (C14H8N2Na requires 227.0585).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,154237-70-4, its application will become more common.
Reference:
Patent; UNIVERSITY OF BATH; THREADGILL, Michael David; LLOYD, Matthew David; THOMPSON, Andrew Spencer; NATHUBHAI, Amit; WOOD, Pauline Joy; PAINE, Helen Angharad; KUMPAN, Ekaterina; SUNDERLAND, Peter Thomas; CHUE YEN WOON, Esther; WO2014/87165; (2014); A1;,
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